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United States Patent 5,506,294
Westerhoff April 9, 1996
Non-volatile material

Abstract

A non-volatile compound useful as a solvent and a method of manufacturing the compound. The compound is formed from heating a combination of a lactide and a drying oil which has conjugated double bonds. The compound is particularly useful as a resin solvent for use with coatings, paints and printing inks. In addition, it can be used as a compatibilizing agent.

Inventors: Westerhoff; David (P.O. Box 1192 Goose Creek La., Middleburg, VA 22117)
Appl. No.: 393913
Filed: February 24, 1995

Current U.S. Class: 524/500; 427/384; 528/357; 549/274; 554/24; 554/30; 554/31
Intern'l Class: C08J 003/00; C08G 063/78; C07D 309/32; C07B 041/12
Field of Search: 554/24,30,31 549/231,274,415,448 528/357 524/500

References Cited
U.S. Patent Documents
2033131Mar., 1936Ellis106/252.
2188882Jan., 1940Clocker549/253.
2623056Dec., 1952Elwell554/30.
3830763Aug., 1974Gillan et al.554/30.
5374743Dec., 1994Thayer et al.549/274.
Foreign Patent Documents
467226Aug., 1950CA.

Primary Examiner: Yoon; Tae
Attorney, Agent or Firm: Whitham, Curtis, Whitham, & McGinn
Parent Case Text


CROSS-REFERENCE TO RELATED APPLICATIONS

This patent application is a continuation-in-part patent application of the U.S. Patent Application having U.S. Ser. No. 08/162,454 filed on Dec. 3, 1993, now U.S. Pat. No. 5,405,935, and the complete contents of that patent application are herein incorporated by reference.
Claims


I claim:

1. A non-volatile material formed by the reaction of a cyclic keto enol tautomer with an oil having at least one conjugated double bond.

2. The non-volatile material of claim 1 wherein said product is formed by reacting 5-25% by weight of said cyclic keto enol tautomer with 75-95% by weight of said oil.

3. A method of producing a non-volatile material, comprising the steps of:

combining a cyclic keto enol tautomer formed from a compound having a two or more carboxylic acid moieties or at least one hydroxy moiety and one carbocylic acid moieties with an oil; and

heating said combination of said cyclic keto enol tautomer and said oil to produce a non-volatile material.

4. A method of using the non-volatile material of claim 1 comprising the step of applying the non-volatile material to a substrate as a varnish.

5. A method of using the non-volatile material of claim 1 comprising the step of incorporating said non-volatile material into a mixture of two or more polymeric compounds as a compatibilizing agent.
Description


DESCRIPTION

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention generally relates to a compound which can be used as a solvent and a method of manufacturing the compound. More particularly, it is directed to a compound which is formed from heating a combination of a lactide and a drying oil which has conjugated double bonds. This compound is non-volatile and is particularly useful as a resin solvent for use with coatings, paints and printing inks. It can also be used as a compatibilizing agent for resins.

2. Description of the Prior Art

The formulations of most oil based coatings, paints and printing inks include a solid resin which is dissolved in a solvent. These compounds often contain other ingredients depending on the intended use and desired characteristics. It is common to add pigments or dyes to obtain colored coatings. It is also known to include additives to determine the characteristics of the coating. Some examples of features which can be adjusted include: the gloss level, the mildew resistance, and the adhesive properties.

Solvents are usually organic compounds and are used to alter the physical properties of a compound. The solvents currently in use are generally volatile, causing them to be evaporated into the ambient air. The volatile organic compounds are a major cause of air pollution and therefore, they are subject to a variety of local, state and federal regulations. These regulations and the potential for stricter regulations in the future have prompted the manufacturers of these products to investigate alternatives to these solvents. Although a variety of alternatives have been developed, the majority possess draw backs which have prevented their adoption for general commercial use. The draw backs of the alternatives include poor solvency, high toxicity, short shelf life and the production of toxic by-products.

SUMMARY OF THE INVENTION

It is therefore an object of the present invention to provide a compound which can be used as a solvent and which is nonvolatile.

It is another object of the present invention to provide a process for the manufacture of a compound which can be used as a solvent and which is non-volatile.

It is another object of this invention to provide a non-volatile solvent which can be used in both water based inks such as gravure printing ink and in organic inks such as lithographic ink.

It is yet another object of this invention to provide a compound which is non-volatile which is useful as a varnish on furniture and other wood products.

It is also an object of the present invention to provide a solvent which can dissolve a broad range of resins and is able to form a film.

It is a further object of this invention to provide a compound which is of low toxicity.

It is another object of this invention to provide a solvent for use in coatings, paints and printing inks which can replace organic compounds.

According to the invention, there is provided a method for manufacturing a compound wherein an alpha hydroxy acid, lactic or glycolic acid is heated to remove all of the water. The heating produces a cyclic keto enol tautomer. For example, in the case of lactic acid, a lactide is produced as the cyclic keto enol tautomer. In the case of lactic acid, a lactide. The lactide is combined with any drying oil which includes conjugated double bonds and the mixture is heated. The resulting product is useful as a solvent and has successfully been combined with a number of resins and other produces.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT OF TIE INVENTION

The process of the present invention produces a compound which is useful as a solvent, for coatings, paints and inks and as a compatibilizing agent. The first step in the production process is to heat a hydroxy carboxylic acid or dicarboxylic acid to a temperature at which all the mechanical water and one mole of chemical water per mole of acid is removed. In the preferred embodiment the acid is lactic add, glycolic acid or alpha hydroxy acid. It is most preferred to use lactic acid. The minimum temperature at which the desired amount of water is removed is approximately 150.degree. C. However, it should be understood that heating temperature and heating conditions (e.g., pressure, volume of hydroxy carboxylic acid, etc.) can be varied within the practice of this invention. The removal of the water from the acid results in the formation of a cyclic keto enol tautomer. If lactic acid is the starting compound, the produce is a lactide which can be represented by one of the following structures: ##STR1## If desired, derivatives of the cyclic keto enol tautomer can be formed by esterification reactions at the site of the hydroxy constituents or by other means. For example, substituted (e.g., halogenated, etc.) and unsubstituted C.sub.1-30 moieties can be added via esterification to form a suitable derivative. The cyclic keto enol tautomer is then combined with a drying oil which has conjugated double bonds.

It is preferred to use approximately 18% by weight of lactide and approximately 82% by weight of a drying oil or a combination of drying oils. However, the amount of lactide or cyclic keto enol tautomer can range from approximately 5% to 25%. The preferred drying oils include linseed oil, tung oil, oiticica oil, soya oil, dehydrated castor oil, other dehydrated vegetable based oils or other commonly known oils. It should be understood that a wide variety of oils having, for example, 5-50 or more carbons with one or more conjugated double bonds may be useful in the practice of this invention.

The combination of the cyclic keto enol tautomer and drying oil is heated to form the non-volatile solvent. It has been found that optimum results can be achieved by heating at temperatures of approximately 220.degree. C. for a period of approximately two hours. It is anticipated that different heating schedules could also be employed (e.g., longer times at lower temperatures and shorter times at higher temperatures). The resultant product is characterized as being a liquid which ranges in color from clear amber to straw. The viscosity of the product was measured in a number two zahn cup and was found to be 19 to 26 seconds.

It has been determined that having small quantities of chromium, iron, or other transition metals, and particularly those having a valence of 3, aids in the formation of the product. Specifically, a superior reaction product is obtained when the cyclic keto enol tautomer and drying oil are combined with less than 100 ppm of a transition metal during heating. Optimal results were obtained when approximately 8-10 ppm of chromium was present or when 6 ppm of iron and 3 ppm of chromium was present. Other combinations of transition metals having low concentrations (e.g., less than 10-20 ppm) may have similar advantages. It has been found that sufficient chromium content for forming the reaction product can be contributed simply by using a stainless steel vessel when heating the cyclic keto enol tautomer and drying oil. By contrast, when a glass reaction vessel was employed, precipitation of solids occurred. A glass reaction vessel might be suitable if a sufficient quantity of chromium salt or other metal complex is added to the reaction mixture.

As an alternative to the two step process of first forming a cyclic keto enol tautomer and then combining the cyclic keto enol tautomer with a drying oil, the reaction product may be formed in a single seep by heating a mixture of a drying oil and a hydroxy carboxylic acid or dicarboxylic acid that is capable of forming a cyclic keto enol tautomer.

This product is useful as a solvent and can be used with resins and printing inks. In addition, it can also be used to compatibilize polypropylene and polystyrene resins which are used in injection molders and extruders. The product also can be used as a varnish on furniture and wood products.

The product of the above described process can be used to dissolve resins. In particular, it has been shown to successfully form solutions with hydrocarbons, phenolics, acrylics, styrene acrylic copolymers and alkyd resins. These compounds were preferably approximately 40% by weight of the solution. The solutions which were formed were clear and were able to form hard durable films which ranged in thickness from 0.5 to 2 mils.

The product can also be used in the manufacture of lithographic printing inks. Table I provides examples of combinations which can be used to produce printing inks. 

    ______________________________________
                   Overprint
                           Sheetfed No
                   varnish web      heat
    ______________________________________
    Solvent replacement (product)
                     65%       28%      37%
    Bodied tung oil  --        25%      20%
    Styrene acrylic copolymer
                     31%       --       --
    Carbon black linseed flush
                     --        45%      40%
    Micro crystalline wax
                     --         2%       1%
    Acrylic resin     4%       --       --
    Talc             --        --        2%
    ______________________________________


The printing inks manufactured using the product, produced as described supra, were found to create a durable hard film and excellent print quality. The drying time of the inks was between nine and fifteen minutes.

The product has been found to be useful in both water based printing inks such as gravure printing ink and in organic inks such as lithographic inks. For example, gravure printing ink formulations including 0.1-5% of the product of this invention and 95-99.9% gravure printing ink. Water based gravure printing inks exhibit an uneven rough visual appearance. The roughness is caused by uneven absorption of ink into the substrate. This has been referred to as galvanizing in the gravure printing industry. The addition of 1 to 5% of the reaction product to a water based alkaline gravure ink eliminates this phenomena and produces a printed result that has a uniform even appearance.

The material can also be incorporated into other water based coatings. The material is water miscible with the addition of an alkaline material until a pH greater than 7.0 is achieved. Ammonium hydroxide is the preferred material for coating applications.

The product of the present invention is also useful as a compatibilizing agent. A mixture of approximately fifty (50) parts of polypropylene, fifty (50) parts of polystyrene and one (1) part of the product was adsorbed on four (4) parts of ethylene propylene styrene terpolymer. The resultant material was extruded to produce a band which as approximately 1.5 millimeters by 12 millimeters. The extruded material was of a uniform consistency and could be bent without breaking. For comparison purposes, the mixture was also prepared without the product and was extruded. This material was not compatibilized and fractured when deformed.

While the invention has been described in terms of the preferred embodiments, those skilled in the art will recognize that the invention can be practiced with modification within the spirit and scope of the appended claims.

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